THE PINETREE
HOSPITALITY RETREAT
An in-person retreat for hospitality operators who want to build brands people love and experiences that scale.
3 Days
10 Operators
All Inclusive
April 14–16, 2026 | Idyllwild, California
| Founding Cohort · Only 10 Spots
3 Days
10 Operators
All Inclusive
April 14–16, 2026 | Idyllwild, California
Founding Cohort · Only 10 Spots
Running hospitality is rewarding but scaling it can feel isolating.
If you operate short-term rentals, cabins, boutique hotels, or experiential stays, you likely relate to this:
You are balancing operations, guest experience, and constant decision-making
You are growing, but without a clear strategic lens or peer group that understands hospitality
You want to scale in a way that protects your energy and your brand
You want more than nightly bookings and lower-margin revenue
Most hospitality operators are moving fast. Very few take the time to step back, refine the experience, and design the business intentionally.
This retreat creates that space.
A small, high-trust REtreat
for hospitality operators
A small, high-trust mastermind for hospitality operators
The Pinetree Hospitality Retreat is a three-day, in-person experience designed for hospitality operators who want to refine how they run, market, and scale their properties.
This is not a conference.
There are no panels, pitches, or passive sessions.
It is a small, intentional group of operators working through real challenges together in the same environment where Pinetree was built.
Everything you need to step back, think clearly, and move forward with confidence.
This retreat is built around real outcomes, not theory.
The Immersive Retreat Experience
Three days of focused sessions built around real hospitality operations, brand-building, and high-margin experiences.
Guided sessions on hospitality branding, experience design, group sales, and operational discipline
Live walkthrough of how Pinetree curates and sells high-margin group and retreat experiences
Practical frameworks for building a brand guests feel connected to
Clear decision-making time to map next moves for your property
The Immersive Retreat Experience
Three days of focused sessions built around real hospitality operations, brand-building, and high-margin experiences.
Guided sessions on hospitality branding, experience design, group sales, and operational discipline
Live walkthrough of how Pinetree curates and sells high-margin group and retreat experiences
Practical frameworks for building a brand guests feel connected to
Clear decision-making time to map next moves for your property
Community & Collaboration
An intentionally small group of hospitality operators.
A curated founding cohort designed for meaningful conversation and shared learning
Peer feedback from operators actively running properties
Relationship-building that extends beyond the retreat
Hospitality & Wellness Immersion
Experience the environment while learning how it works.
Full access to Pinetree amenities including heated pool, sauna, cold plunges, pickleball court, and communal spaces
Time built into the schedule for movement, recovery, and reflection
Mountain surroundings that create space for clarity and focused thinking
Hospitality & Wellness Immersion
Experience the environment while learning how it works.
Full access to Pinetree amenities including heated pool, sauna, cold plunges, pickleball court, and communal spaces
Time built into the schedule for movement, recovery, and reflection
Mountain surroundings that create space for clarity and focused thinking
Community & Collaboration
An intentionally small group of hospitality operators.
A curated founding cohort designed for meaningful conversation and shared learning
Peer feedback from operators actively running properties
Relationship-building that extends beyond the retreat
WHAT YOU WILL GET
Lodging included for the full retreat
All meals included
Curated reels and content creation so you can share the experience without filming or posting yourself
Full access to Pinetree amenities including sauna, cold plunge, pickleball court, and communal spaces
All retreat sessions, workshops, and group discussions
Arrival April 14 and departure by noon on April 16
GET TODAY FOR ONLY
$2,500
OR 50% deposit ($1,250) with balance due March 15. Non-Refundable
WHO THIS IS FOR
This retreat is designed for active hospitality operators.
A short-term rental operator
A boutique hotel owner
A cabin, lodge, glamping, or retreat property owner
A hospitality founder looking to expand beyond nightly bookings
Interested in brand-led growth and group sales
Creators building lifestyle-driven hospitality brands
You do not need to be large.
You do need to be operating and open to refining how you do business.
WHO THIS IS FOR
This mastermind is designed for operators, not beginners.
A short-term rental operator
A boutique hotel owner
A cabin, lodge, glamping, or retreat property owner
A hospitality founder looking to expand beyond nightly bookings
Interested in brand-led growth and group sales
Creators building lifestyle-driven hospitality brands
You do not need to be large.
You do need to be operating and open to refining how you do business.
WHEN & WHERE
Monday, April 14
Arrival and check-in from 3:00 to 8:00 PM
Welcome dinner at 7:00 PM
Tuesday, April 15
Optional morning workout
Sauna and cold plunge
Hot seat sessions
Deep work and guided discussions
Pickleball tournament
Group dinner
Wednesday, April 16
Optional morning hike, sauna, and cold plunge
Final session focused on decisions and next moves
Departure by noon
This is an all-inclusive retreat covering lodging, food, sessions, and content creation.
Investment details are shared after application to ensure the right group fit.
Spots are limited.
WHEN & WHERE
Monday, April 14
Arrival and check-in from 3:00 to 8:00 PM
Welcome dinner at 7:00 PM
Tuesday, April 15
Optional morning workout
Sauna and cold plunge
Hot seat sessions
Deep work and guided discussions
Pickleball tournament
Group dinner
Wednesday, April 16
Optional morning hike, sauna, and cold plunge
Final session focused on decisions and next moves
Departure by noon
This is an all-inclusive retreat covering lodging, food, sessions, and content creation. Investment details are shared after application to ensure the right group fit.
Spots are limited.
Frequently asked questions (FAQs)
Is lodging included?
Yes. Lodging is included for the full retreat, from arrival on April 14 through departure on April 16.
Are meals included?
Yes. Intimate by design. This is not a conference — it’s a curated cohort.
What time is arrival and departure?
Arrival and check-in are on Monday, April 14 from 3:00 to 8:00 PM.
Departure is by noon on Wednesday, April 16.
Who is this retreat for?
Yes, but they must apply separately. Each attendee requires their own seat.
How many spots are available?
Spots are intentionally limited to 10 to maintain a high-quality, focused experience. Group size is small by design.
How does the application process work?
After you apply, our team will review your application within 24–48 hours. If approved, you’ll receive details on how to secure your spot.
Is the retreat refundable?
No. Due to limited capacity and included lodging and meals, all payments are non-refundable.
Can I bring a business partner or team member?
Yes, but each attendee must submit their own application and be approved separately. Please reach out to us at for shared accommodation.
Will content be created during the retreat?
Yes. Curated reels and content will be captured so you can share the experience without needing to film or post yourself.
Will there be time to relax or enjoy the property?
Yes. The schedule intentionally includes wellness activities and open time to enjoy Pinetree’s amenities, including sauna, cold plunge, pickleball court, heated pool and beautiful scenery all around the property.
What should I bring?
After approval, you’ll receive a detailed welcome email with what to pack, how to prepare, and what to expect during the retreat.
What if spots are full?
If the retreat is full, you’ll have the option to join the waitlist and be first to hear about future PineTree retreats.
Apply to Join the PineTree Hospitality Retreat
Limited to 10 Hospitality Operators | April 14–16, 2026 at Idyllwild, California
This retreat is intentionally small to preserve depth, conversation, and quality.
If you want to refine your hospitality business and build experiences that last, apply below.
Applications are reviewed manually.
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